3-Iodotoluene → HCID 22049098, compound

HRID 2087225Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5](N2C3C(=CC=CC=3)C=C2)=[CH:4][CH:3]=1.[NH:17]1[C:25]2[C:20](=[CH:21][C:22]([CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([C:33]4[CH:34]=[C:35]([NH:39][C:40](=[O:44])[CH:41]([CH3:43])[CH3:42])[CH:36]=[CH:37][CH:38]=4)[CH2:29][CH2:28]3)=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.IC1C=CC=C(C)C=1>>[CH3:43][CH:41]([CH3:42])[C:40]([NH:39][C:35]1[CH:36]=[CH:37][CH:38]=[C:33]([CH:30]2[CH2:31][CH2:32][N:27]([CH2:26][C:22]3[CH:21]=[C:20]4[C:25](=[CH:24][CH:23]=3)[N:17]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[CH:18]=[CH:19]4)[CH2:28][CH2:29]2)[CH:34]=1)=[O:44]

Participants

Reactant 3

HCID 122683-Iodotoluene

HCID 9794286N-(4-methylphenyl)indole

HCID 22049334N-{3-[1-(1H-indol-5-ylmethyl)-4-piperidinyl]phenyl)-2-methylpropanamide

Product 1

HCID 22049098HCID 22049098, compoundYield 60%

Procedure

According to the procedure used for the synthesis of 1-(4-methylphenyl)1H-indole, N-{3-[1-(1H-indol-5-ylmethyl)-4-piperidinyl]phenyl}-2-methylpropanamide (37.5 mg, 0.100 mmol) and 1-iodo-3-methylbenzene (43.6 mg, 0.200 mmol) gave the desired product (28 mg, 60%). 1H NMR (400 MHz, CDCl3) δ 7.68-6.60 (m, 14H), 3.66 (s, 2H), 3.16-2.96 (m, 2H), 2.59-2.44 (m, 2H), 2.44 (s, 3H), 2.18-2.01 (m, 2H), 1.91-1.68 (m, 4H), 1.24 (d, 6H, J=6.8 Hz); ESMS m/e: 466.2 (M+H)+.

Sources & evidence

ORD record: ord-4004a7f768b242cdb8b1be3897af4208
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727264B1

Reaction notes

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